Sodium Carbonate → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-methoxy-5-methyl-3-thienyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (Intermediate 21, 13 mg; 0.0219 mmol) was treated with (2-methoxy-5-methyl-3-thienyl)boronic acid (Step C, 10.4 mg; 0.0657 mmol), tetrakis(triphenylphosphine)palladium (0) (3 mg; 0.0026 mmol), and sodium carbonate (20 mg) as described in Example 291 to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-methoxy-5-methyl-3-thienyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one as a yellow glass. LCMS=598.2 (M+1)+. 1H NMR (benzene-d6, 500 MHz): δ 7.75 (s, 1 H), 7.57 (s, 1 H), 7.31-29 (m, 1H), 7.24 (s, 2 H), 7.12-7.10 (m, 1 H), 6.14 (s, 1 H), 4.96 (d, J=16 Hz, 1 H), 4.57 (d, J=8 Hz, 1 H), 3.99 (d, J=15.8 Hz, 1 H), 3.30 (s, 3 H), 2.95-2.92 (m, 1 H), 2.05 (s, 3 H), −0.28 (d, J=6.7 Hz, 3 H).

Provenance & Evidence